William Romme received funding to build the umbrella plane after his concept won a 1910 aircraft design contest, either because it was one of those contests where "everyone's a winner!" or because the only other entrant was Horatio Phillips, who just hot-glued massive piles of randomly distributed wings to a sewing machine.
Romme's prototype, as you can see, consisted of little more than a disclike wooden frame with canvas draped over the front, taking its design cues from the humble umbrella. Evidently having never handled nor seen an umbrella in real life, Romme was flabbergasted when the flimsy plane was flipped over by the wind during a test run. The plane was badly damaged, and the engineer learned a valuable lesson ... which he promptly forgot, and then built another plane just like the first. This model was slightly more successful, soaring to a dizzying height of 15 feet before presumably folding inside out and whipping down the street to get run over by a bus.
"If at first you don't succeed, repeat the same mistake over and over again."
Italian aeronautical engineer Luigi Stipa presumably designed the Stipa-Caproni in 1932 on a drunken bet that he could make an empty beer can fly. It was a bet he won: The Stipa-Caproni was so stable in flight that you couldn't actually turn the damn thing, which is kind of an integral part of flying, as very few airports simply point you toward your destination and wish you Godspeed.
"If you get to the ocean, you've gone too far. Just bail out and we'll find you."
It wasn't Stipa's fault, though: His primary interest was in demonstrating the efficiency of the engine prototype, and it actually succeeded in that regard well beyond expectations. It's just that, like all eccentric geniuses, he got so focused on getting one thing perfect that he plain forgot to bring the rest of the plane. The end result was a brilliant, stable, efficient new power source ... with two stubby wings plugged into each side and a pilot comically strapped directly on top of the engine like Slim Pickens in Dr. Strangelove.
"Uh, hey ... Ground Control? I think someone circumcised my plane."
The Stipa-Caproni was a universally terrible plane, but the concept was sound; it is commonly believed that Stipa's design was the inspiration for the modern jet engine. That's right: That flying garbage disposal up there was the great-granddaddy of those bitchin' fighter planes from Top Gun.